Founding AI Engineer | Build the Future of Insurance Intelligence

Insurance still runs on 100+ page documents written by lawyers, for lawyers — and professionals spend endless hours comparing them line by line.

We’re changing that with cutting-edge AI that makes these complex documents readable by both humans and machines.

As our Founding AI Engineer, you’ll architect LLM systems that can understand nuanced legal language better than most attorneys — transforming how the world’s largest insurance brokers make critical decisions.

This isn’t about building chatbots. It’s about creating reasoning AI that can interpret coverage, identify gaps, and rethink how a $1.4T industry operates.

What You’ll Do

You’ll own and evolve a production LLM application stack — designing intelligent, high-performing systems that push beyond basic RAG implementations.

Architect sophisticated LLM workflows for complex policy interpretation
Build multi-step reasoning agents and decision-making systems
Develop evaluation frameworks, monitoring tools, and cost-optimization pipelines
Master vector databases and semantic search for legal and insurance data

About You

Proven experience building and deploying advanced LLM applications
Deep understanding of prompt engineering, agentic systems, and evaluation frameworks
Strong background with LangChain, LlamaIndex, or similar
Thrive in founder-led, fast-moving environments where you take full ownership
Passionate about solving real-world challenges with meaningful impact

This is an opportunity to define the AI foundation of a venture-backed startup working with several of the largest US insurance brokers.

We’re looking for someone exceptional — and willing to wait for the right person.

Location: Hybrid if you are based in Chicago. Remote if you are based in either New York/ San Francisco.

Must be a US citizen or Green card holder.

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